This article originally appeared in the December 2009 issue

Look around a skippers’ meeting at a typical regatta and you’ll see all the usual suspects: seasoned salts, their families and a smattering of recent college grads or young adults sampling the sailing culture. The same folks populate most charter bases and destinations, which makes sense, considering the means and experience that chartering requires.

You can imagine the surprise, then, of the folks at TMM in Tortola, BVI, and again of Brian Blank at Barefoot Charters in Newport, Rhode Island when we showed up. Fresh out of college, our motley crew arrived in tie-dyed shirts, flippy-floppies and provisions from Costco. We were bursting with excitement as we gripped our sailing resumes, which were deemed sufficient, but barely. A couple of our crew had been on charter boats dozens of times and everyone else was keen to learn. I’m sure our charter directors had their misgivings, but like a hesitant father handing over the keys for the first time, they crossed their fingers and set us loose.

Thank goodness. Both trips were full of excellent sailing and fantastic memories that will serve as a jumping-off point for many charters to come. But in watching Blank’s attitude toward us turn from nervous to proud, I was reminded of the chasm between college sailors (where our crew met) and more seasoned seafarers. There are many ways in which the sailing community could bridge this gap, and encouraging young people to charter boats is a great place to start.

Chartering doesn’t have to be for the thick-walleted or the super-experienced. As Andrew Waters at Conch Charters points out, a charter boat comes at a set cost, so the more friends you’re willing to squeeze onboard, the cheaper it is for everyone. He even suggests rigging a two-man tent on a catamaran’s trampoline to optimize sleeping space. “If a group of young people is willing to be flexible with their sleeping arrangements, we’ll help them get the right boat at the right price, and they could get the holiday of a lifetime,” says Waters.

As for the experience part of the equation, Sunsail’s Josie Tucci reminded me that there are many ways to make sailing less intimidating for young charterers, such as flotillas, sailing schools and captained yachts. “Sailing on a flotilla is an easy way to enjoy a sailing vacation with the freedom to do as you please, but the comfort of knowing there’s help on hand,” she says. “It offers a balance of independence and support.”

My crew and I are lucky to have stumbled upon chartering at such a young age. The more we charter, the more we see how delightful (and doable) it actually is. If you or your kids have been searching for a way to narrow the age gap, this holiday season is as good a time as any to send them on their first trip and watch as they fall in love with chartering.

Tell them to look for the boat full of tie-dye shirts and flippy-floppies. We’ll be awaiting their arrival.